Sodium borohydride → Methyl-4-acetylamino-3-hydroxymethylbenzoate

Participants

Reaction Conditions

Reaction Steps

Methyl-4-acetylamino-3-formylbenzoate (Gassman, P. G.; Drews, H. R. J. Am. Chem. Soc. 1978, 100, 7600-7610) (0.331 g, 0.0015 mol) was dissolved in methanol (5 mL) and cooled to 0° C. Sodium borohydride (0.057 g, 0.0015 mol) was added to the above solution at 0° C. and stirred for 0.25 h. The reaction was complete by TLC during this time. It was neutralized with H+ resin, filtered, and the filtrate concentrated. The residue was dried under vacuum over phosphorus pentoxide at 56° C. to give 0.33 g (99%) of methyl-4-acetylamino-3-hydroxymethylbenzoate as a pink solid, mp 60° C.

Provenance & Evidence